Sodium Hydroxide → HCID 11673768, compound

HRID 1754484Notes

Reaction equation

HRID 1754484 reaction equation
[CH3:1][C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH2:21][C:22]([OH:24])=[O:23].[OH-].[Na+].COC(=O)CC1C2C(=NC=CC=2)N(CC2C=CC([N+]([O-])=O)=CC=2)C=1C>C1COCC1.CO>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:10]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[C:3]([CH2:21][C:22]([OH:24])=[O:23])=[C:2]2[CH3:1])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67218923HCID 67218923, compoundHCID 67219255HCID 67219255, compound

Product 1

HCID 11673768HCID 11673768, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

[2-Methyl-1-(4-nitro-benzyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid: 1M Aqueous NaOH (1.18 ml) is added to a stirring suspension of [2-methyl-1-(4-nitro-benzyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (0.2 g, 0.54 mmol) in 4:1 THF/MeOH (5 ml). The reaction mixture is allowed to stir at room temperature for 4 hours and then the solvent is removed in vacuo. The crude residue is dissolved in 1:1 THF/water and acidified to pH 3-4 using 6M HCl. After stirring for 30 minutes the resulting suspension is filtered and dried in vacuo at 110° C. to yield the titled product as a yellow solid. (MH+326)

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe crude residue is dissolved in 1:1 THF/water
  3. stirringAfter stirring for 30 minutes the resulting suspension
  4. filtrationis filtered
  5. customdried in vacuo at 110° C.

Sources & evidence

ORD record
ord-bff1d1270b234e8ab8eebdc71f5749f3
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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